Posted on January 7, 2021 by Sheery — 2 Comments

 

Can't you tell I'm a bisexual crossdresser

One of the reasons I enjoy writing this blog is that it serves as a diary of sorts. It is usually while slipping into my lady things and feeling the feminine vibes and then getting my inspiration into words. I also have a separate little black journal I write to although it is not quite as extensive in my (perverse) thoughts as it is here. The journal is also a lot harder to hide from people in case I’m dumb enough to leave it on the coffee table, which tends to happen on occasion.

(Note that you may have noticed a lapse in time last year. Just assume I was macho me the whole time, OK?)

Having this blog means I even like to go back and read my own writing to see what I was thinking about at some random point in time in the past, which tends to amuse me today. I ran across one entry in particular about my evolving bi-curious nature, though, which I felt the need to revisit since my sexuality has taken quite the detour from nearly ten years ago.

Back then I was coming to terms that I was wanting more than just “vanilla” hetero relationships and felt an urge to explore my sexuality. from the perspective of a woman, or kind of like one at least. I didn’t want to just dress up. I wanted to be the woman that gives the blowjob or takes a good pounding (albeit from the rear). It felt sexy and exciting to fantasize about it, plus it went everything against my rather conservative upbringing which just made it all the more exciting.

I asked, I received.

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Posted on December 29, 2020 by Sheery — 2 Comments

Sheery wearing an Oroblu bodysuit and Wolford Neon tights

I often times think about how my crossdressing has evolved over the years. Well, maybe even my whole life. More than two thirds of it, I’d say, I desperately tried all I could to keep it a secret. It was something I would do every now and then in private just to get my kicks and then get on with my day. I guess I thought of it back then as just some of my “weird” tendencies.

Yet back then, it was only about slipping into pantyhose which eventually led to slipping on lingerie along with it. I knew that only made me a male in women’s underwear since I surely didn’t look the part of anything female. It was enjoyable and satisfying nonetheless. Those “taboo” articles of clothing made it oh so alluring to drape it on my body and pretend I was female in some perverted sort of way. At least that was how I thought of it back then.

Today, however, my own crossdressing has evolved to a point where I couldn’t have imagined even ten years ago. No more am I the male pantyboy (or more like the resident pantyhoseboy). Instead I have incorporated more “girlyness” into my everyday lifestyle. For example, I shave all body hair (even my face!) and keep my fingernails and toenails perfectly trimmed with my toenails nearly almost always painted. Then there is that subtle dot of perfume that I like to put right over my deodorant in the morning.

I don’t exactly give myself away entirely as little miss me but I do absolutely enjoy giving away a hint of my feminine side whenever I can. And each day it is a little bit more than the last.

I am always left thinking, though, what will I be like ten years from now if I keep going in this direction?

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Posted on June 4, 2020 by Sheery — 1 Comment

Me in Wolford Moonlight Sleeves

Normally I’m all about whatever Wolford makes, like you know those Neon 40 tights. It shouldn’t be a surprise that I’m signed up for their newsletter, have a Wolford branded makeup bag and now a nice little collection of tights, bodysuits, bras, panties… you get the idea. So one day, while browsing their website to their new additions, I came across something that was somewhat hard to fathom, especially for them.

Is that pantyhose for the arms I see? They look like long gloves (which I also love) but not covering the hands, AKA sleeves.

OK, well, time to buy these and check them out for myself.

Then they come. I rip the little boxes open and slip one of these suckers on my left arm. Then the other on the right arm.

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Posted on March 18, 2020 by Sheery — No Comments

Sheery in teddy and tights

If you’re like me (of course you are), then after all those years of slipping into your favorite pantyhose and lingerie, you have those few items that you have and will always love forever. By the way, I estimate I have worn approximately 500 pairs of pantyhose and around 200 pieces of lingerie in my lifetime. Yet there are only a few items that I still have that are very dear to my heart.

Note that I’m not talking pantyhose here. Don’t get me wrong, they are my first love and I still have my very first pair of Wolford Neon 40 on display in my bedroom (now too worn to wear). Lingerie, however the complement to my beloved  legwear they may be, is still a valued treasure in my book though.

So back to that lingerie. To the day there is that one very piece I continue to wear, a black Victoria’s Secret teddy, purchased five years ago on a whim. It was one of those rare purchases that was actually much better when you have and hold it than what you see in pictures before buying. And what a beautiful teddy it was.

I usually have issues with wearing teddies being they are too constrictive and/or the fit is off or, worse, it just plain looks bad. I get it. They are not made for men or an effeminate one at that. However, this one, while coming out of the package looking very teeny weeny tiny, actually fit to perfection. Not only that, but there were no restrictions in movement whatsoever. In other words, it was nice and comfortable. Up until now, a comfortable teddy was practically a paradox.

But comfort is just a small part of the equation. How it looks, at least to yourself, is what really counts doesn’t it?

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Posted on January 12, 2020 by Sheery — No Comments
Like my new bustier?

NOTE: I know it’s been a while since I posted here. Let’s just say a lot of life has happened between 2018 and now. I’ve thought about closing up shop here during this time but, you know what? I’m still a crossdresser and, to be honest, I am now more than ever. Like really seriously into it 😉

A couple months ago, I did a Google search for a particular (feminine) garment I was interested in (can’t remember what it was though) and I came across a new website I’ve never seen or heard of ever, Vinted. That garment was for sale brand new at a price that I thought was rather low. Well, I didn’t happen to buy it but I did spend a good couple of hours browsing around in there. The OMG moment finally came around.

If you’re not familiar with Vinted, it’s more or less a website that promotes clearing out your mass of unused clothing and/or buying it from someone else who wants to clear out their rejected threads. It’s almost identical to eBay in a way, however, eBay is, really, too hard to find what you are looking for. Vinted is pretty much just for finding clothing and that’s it.

In the nearly two months that I’ve used Vinted, I’ve been obsessed with it. I’ve not only found awesome second hand clothing but also new items still with tags that people just happen to have sitting around. What a concept!

Of course, I could have looked around and shop for regular male clothes but, hell no! I went after all the womens’ wear that I have always been dreaming about draping over my body. Miniskirts, bodysuits, lingerie and of course my most sought out items… anything Wolford.

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Posted on June 17, 2018 by Sheery — 6 Comments

Sheery in denim mini and Wolford tights

While I can’t speak for all crossdressers out there, I firmly believe that eventually a line gets crossed where one goes from the occasional pantyhose-under-the-jeans to the full-on appearing (more) like a woman. Or, at least hoping to appear like one.

Calling it growing up or hitting puberty if you will. Really, there are those little things you do just like a little teeny-bopper girl. Shave your legs and armpits (and beard A LOT more), exfoliate and lotion all over, manicures, pedicures, etc, etc. They not only make you look more feminine but FEEL more feminine as well. And feeling more feminine makes you act more feminine, too, which is kind of the end goal of this whole crossdressing thing. Well, in my book anyway.

One way I found to validate myself as a crossdresser was to have at least have a decent photo. That is definitely the hardest thing to do since you either have to hire a friend or photographer to do the deed or learn how to use the auto feature on your own camera. Then, of course, the most important part: the pose.

There is always the easy way out… taking a selfie or a mirror-selfie. How lame is that, though, since the selfie is so ubiquitous that they are really hardly even noticed. Maybe one here or there is OK, but if a portrait collection consists of only selfie photos,  then why even bother?

I know I’m being a bit snotty but, coming from a crossdresser who has taken many a bad photo and has quite the collection to prove it, having a good photo of yourself where someone viewing it has to ask, “Man or woman?” is the ultimate joy of growing into my own feminine self.

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Posted on May 27, 2018 by Sheery — No Comments

Item m6 bodysuit, rear view

While I do have some bodysuits in my vast collection of lingerie, I only have the ones that lightly drape over my body, kind of like a leotard. For the most part, they are comfortable and perfect for lounging around as feminine me. Then there are those bodysuits that are strictly for shaping, tightening you up in all those loose places. Those, however, tend to make me feel like a sausage and look like someone out of a 80’s Sears catalog.

One day, in my occasional lingerie browsing, I came across a bodysuit that looked incredible (of course on a female model) but was a shaper type. Normally that makes me look on but I couldn’t take my eye off of this, the Item m6 Shape String Body. It appeared somewhat like a swimsuit but was a typical style I normally like in a non-shaping bodysuit.

Regardless, I bought one… and was quite surprised by what I slipped into.

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Posted on April 8, 2018 by Sheery — 4 Comments

Sheery in Fogal Rapallo pantyhose

I recently had an epiphany about my whole crossdressing life up until now. Primarily, I’m no longer a little teenie-bopper sneaking around with my stash of girly goodies waiting eagerly for a chance to slip into some pantyhose in my room with the door locked. Those days are LONG past. Yet, given how long it was ago, I can still remember my dress sessions rather vividly, as if it were my first time driving.

I’m not afraid to admit it to myself that crossdressing is deeply rooted part of my personality. I love it, have an inredible passion in it and, well, I just happen to like throwing on a pair of pantyhose and getting off on it… for the last few decades. Is there really any harm in it? Ok, so maybe getting a snag in the nylons but that’s another story.

I find it of interest in my self-assessment, however, that crossdressing is obviously ingrained in my own sexuality. Before you go all Captain Obvious here, think about it. Man throws on pantyhose, some lingerie and maybe a wig and a little makeup. Then dot some perfume on for good measure before stepping into those heels. Typical crossdresser duties and was actually what I did just an hour ago.

Yet that’s where the silky things end and crossdresser me takes the stage. All five senses are heightened (yes, I can taste the “fruit” from my lipstick), arousal is taking it’s shape and I NEED, right then and there, to be missy me. No longer am I the weird dude with the feminine tendencies but rather a transformed me with feminine desires and feelings. And those desires now have to be met.

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Posted on February 25, 2018 by Sheery — 6 Comments

Me in Wolford Neon 40 in Fairly Light

How many times do I have to say it? I love Wolford Neon 40 with a big fat exclamation mark. The most gorgeously shiny tights ever made are the hallmark of every crossdresser’s little drawer of silkies. In case you’re a crossdresser or have a pantyhose kink and been in a hole for the last twenty years, here is a little primer on Wolford Neon tights.

It’s also probably safe to say that the go-to choice for color is the lovely Gobi, so beautiful on the legs like it’s namesake hot sands of Mongolia. Personally, I have an old worn pair in Gobi from more than ten years ago and more recently updated my stash to a more pristine pair. An absolute must when the urge to drown your legs in pantyhose overcomes you and you think why not just treat yourself to a bit of caviar this time.

Wolford typically has the Neon 40 in their black and brown variants and then the skin-tone shades of Cosmetic (the lightest tone) and the already mentioned coppery gold Gobi. Then, to round things out, seasonal fashiony shades that only appear for one season. Visiting the website not too long ago, I noticed they had a new color, Fairly Light, but with no image available for a preview (at this time still none!).

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Posted on January 13, 2018 by Sheery — 5 Comments

Rumpy Butt Plug

I’m not afraid to admit that I like to get it on… alone. Hey, it’s actually healthy for the sex life to keep the juices flowing and release all that tension when needed. In fact, a lot of you out there seem to agree since my most popular post is some ideas for your kinky mastubation. So I’m not alone here in liking to get down and dirty without the typical wake and wank. A little creative masturbation can actually be quite a thrill.

Hence, I came upon (literally) a new little friend of mine, the Rumpy Butt Plug. You can see, it’s not your average drain stopper, actually looking more like a fat dildo. And so there is nothing like putting a new toy to test, especially one that looks like it can tear quite a hole in you and then some.

The Rumpy has quite the dimensions for a plug: 6 inches (15 cm) of insertable pleasure, 2.25 inches (5.7 cm) in diameter of the large bulb and roughly 1.75 inches (4.5 cm) in diameter of the large penis-like head. It’s nice and smooth with no rough spots or edges and made of a soft PVC that has some flex to it. A pretty sight it is!

Now for the trial. To get into the mood, I slip into some hold up stockings and a bra and a little perfume to top it off. Then I lube up the Rumpy and my asshole very well and attempt to get that bad boy inside. The head of the plug slipped in after a few pushes and gave me quite the jolt when it did. It definitely is unlike anything I ever put up my ass before and I’m thinking with wide eyes “This thing is no joke!”

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